Isatoic Anhydride → 2-amino-N-(4-fluorophenyl)benzamide
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)O[C:10]2=[O:11]>CN(C)C=O.C(OCC)(=O)C>[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=1[C:10]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)=[O:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 115 °C
Procedure
To a solution of 4-fluoroaniline (2.40 mL, 24.5 mmol) in N,N-dimethylformamide (30 mL) was added isatoic anhydride (4.00 g, 24.5 mmol), and the reaction mixture was heated at 115° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The organic layer was washed with 1 N NaOH (200 mL), water (100 mL), then brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent) to give 2-amino-N-(4-fluoro-phenyl)-benzamide as white solid. Yield: 2.00 g (35%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washThe organic layer was washed with 1 N NaOH (200 mL), water (100 mL)
- dry with materialbrine, and dried over Na2SO4
- customThe solvent was removed under reduced pressure
- customto give crude product, which
- customwas purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent)
Sources & evidence
- ORD record
- ord-561afb952a3f4ecdaddd8828deba7729
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952021B2
Reaction notes
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